Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: Tetraorganosilanes for the practical cross-coupling reaction

Abstract

Readily accessible and highly stable alkenyl- and aryl[2-(hydroxymethyl)-phenyl]dimethylsilanes cross-couple with various aryl and alkenyl halides under mild reac-tion conditions employing K2CO3as a base at 35–80 °C. The reaction tolerates a diverserange of functional groups including silyl protections. The silicon residue, cyclic silyl ether,is readily recovered and reused on a gram-scale synthesis. Intramolecular coordination of aproximal hydroxyl group is considered to efficiently form pentacoordinated silicates havinga transferable group at an axial position.